4 Times Michael impresses Jan and 1 Time Jan impresses Michael
by sarameyester
Summary: It's exactly as the title says. However, I have to make this into a chapter fic because it is just that long. Takes place before, during and after Michael and Jan go to Jamaica. Please read and review!
1. Jan says 'yes'

AUTHOR NOTE: I'll try and make this quick. It's been so long since I've written about this beautiful couple. I miss writing so much and figured a good way to get back into it would be by writing fanfiction again.

That being said-here's what you need to know about this fic. A lot of it will be AU but I still tried to keep some parts like the show and some parts like what could've actually happened. What started out as a "5 Times" fic, turned into a much rather long piece, that's why it's most definitely a chapter story.

Setting: This takes place after Michael asks Jan to go to Jamaica with him.

Oh and please let me know what you thought! Makes my day!

It's Friday night, the day before Christmas Eve. Jan is still at work because they're having their annual Christmas party. However, she isn't necessarily "partying". She was trying to finish some work before leaving for her vacation. She's more than happy she was in her office otherwise she would've missed Michael's phone call.

Now, Jan sits in silence trying to process what just happened. She's still surprised at how easy it was to say _yes._ There was no hesitation and no fear of losing her job. Okay well yes, she is a _little_ worried what they'll say but she'll be sure to read over the contract very carefully...just to make sure this isn't too risky.

Michael inviting her was the perfect sign she was looking for. She just had a session with her psychiatrist the day before. And as always, the subject of Michael came up. She, since probably Chili's, has been fighting these so-called feelings towards Michael. She couldn't bring herself to admit that she was attracted to him. She sorta hoped these _feelings_ were just that. Feelings. Something that would eventually go away. Something that was just a crush. She was wrong…she was dead wrong. Because she just said yes...because he just invited her. She instantly started daydreaming about them in Jamaica and fantasizing about things they're gonna do. Well… _hopefully_ do. She tries holding back a smile-afraid someone would see her.

Jan is actually _supposed_ to be going to Scottsdale to visit her sister. She's more nervous canceling her trip to her sisters' last minute than she is taking this impromptu trip with Michael. She takes a deep breath while shaking those thoughts out of her head. She knows her sister will understand.

"Hey Julie. Do you have a minute?"

"Hey Janet-what's up?"

Jan takes a deep breath, "I'm so sorry to do this, but something came up."

"Oh no! You're canceling? The day before you leave? Jan! Peyton is gonna be so crushed."

"I know. I know but something huge happened and I hope you understand why I have to do this."

"What's going on?"

"He invited me to Jamaica with him, Julie." The tone in her voice told her sister that she was indeed grinning. Yet, not hearing a word in response makes Jan continue, "I mean…I have to do this, right Jules? I've been waiting for some sign telling me to jump and this is as clear as it can get. Of course it had to happen now. I'm so sorry. Please tell Peyton that I'll come down in a month or two. I promise. I just…"

"It's okay, Jan. Calm down. You're right, you have to do this. You deserve to be happy, you know? Especially since Richard was such an asshole."

"Thank you so much for understanding. You have no idea how nervous I was to tell you."

"So how in the world did this happen? I mean, taking a trip together to a romantic place when you aren't even together? Isn't it crazy? Even for you?"

"Well, yes and no. I mean we kind of have a history and there's definitely a different kind of tension between us. I mean-I don't know-it's kind of a huge risk since my job is at stake. If anyone finds-"

"Wait. What? Why is your…do you work with this man? Oh my god, he's your boss! This is why you've never really said where he worked. Jan! You have to be careful!"

"Oh my god, Julie! He is most certainly _not_ my boss, okay?" Jan takes a deep breath as her sister waits for her to continue. "I'm _his_ boss."

"Oh my god…that's worse." All Julie can do is laugh.

"Yeah, you're probably right. Well listen-again, I am so sorry...I will be sure to make it up to you and Peyton."

"Have fun, Jan. Oh! And I want to know all the details. Well...almost all."

Michael is reclining back in his office chair...hands behind his head...feet up on his desk...grinning from ear to ear...not caring who notices.

Michael just asked his boss to join him in Jamaica! And she said yes. Without hesitation even. In fact, he hardly was able to finish his question before she figures he should probably play it safe, though, and not expect anything (i.e. sex) since Jan said once that nothing will ever happen between them. He's sure that she only desperately agreed because she needs to get away. She would've said _yes_ to anyone. However, this could be his chance to prove to her that he's not all that bad.

Michael knew he always had a thing for Jan. That whole _'will they...won't they', 'on again...off again'_ relationship. He thought of them as the Ross and Rachel couple of the office. No one else would ever view them as that couple because well, Ross and Rachel actually _had_ a relationship and actually _had_ sex. This is all irrelevant anyways because he already decided to play it safe and not expect sex. A real friendship would be amazing. _Friends with benefits._ He giggles as he shakes his head and picks up the phone again.

"Michael?"

"Mi madre! Que pasa?"

"Do you have any idea what time it is?"

"Oh I'm sorry! I forgot-you old people like to go to bed at 6:30"

"For the hundredth time, I don't go to bed at 6:30. Michael, dear, what's going on anyway?"

"I did it Mom! I finally did it! And she said yes…finally! She finally said yes-can you believe it?"

"I'm not following…"

"We're going to Jamaica. The most beautiful place on this planet. And I'm going with her."

"Don't you think it's a little soon, Michael? How long have you even been together?"

"Well, I guess we're kind of _not_ together. I don't know…it's complicated."

"You're not talking about that _Carol_ you were dating?"

"Oh! Yeah…no. That ended like ages ago. Or, well like 8 hours ago."

"Oh my god, this is a lot of information to process at 11:00 at night."

"I invited Jan!"

"You what? Oh my god, Michael! You have to be careful. She is your boss. If and when this-thing-ends, life around the office is gonna suck. Seeing each other is going to suck. And when-"

"It's okay Mom! It's not going to end because nothing is going to start. We're just going together as-as friends."

"Yeah, right. Like that's your _only_ intention?"

"Scouts honor."

"Okay well have fun and I-uh-let me know how it goes. Love you Mikey. Oh and don't call me this late again…unless it's a life or death emergency."


	2. Michael doesn't expect sex

1-Michael isn't expecting anything from Jan

Jan arrives at Michaels condo. It's quite late but they agreed that she'd spend the night there since their flight leaves Philadelphia at 6am.

"Oh my god, am I dreaming or is Jan Levinson actually on my door step?" Michael laughs in amazement and lets her in.

Jan clears her throat as she walks in, "thank you Michael."

"Oh and it sounds like you brought corporate Jan with you. Awesome."

Jan senses his sarcasm and tries to relax a little. She really wasn't _trying_ to sound corporate. I mean, they're going to be doing a lot of unprofessional things together this week. She'd rather have it not be awkward.

"I'm sorry, I think it's just a force of habit. Maybe nerves? I don't know." Jan rolls her eyes at herself for acting so uptight.

"No need to be nervous Jan." Michael helps Jan slip her jacket off which sends shivers down spine. "Merry Christmas Eve, by the way."

"Oh! Merry Christmas Eve. It doesn't feel like Christmas."

"I know. So why are you nervous? You should be anything but nervous-laying out in the sun all day? Sipping on fruity drinks? Doesn't sound nerve wrecking to me."

"You're not nervous about going together?"

"Not at all. It's not like anyone's going to see us there. Besides-I just thought you'd want to be by yourself and enjoy some peace and quiet. You always look like you need a vacation."

"Ah. I just thought..." _It amazes me that he doesn't think about me the way I think about him._ Jan is a little impressed that he might just be looking for a friend this week. He's probably just playing it safe since she _is_ his boss after all. Smart move, Michael Scott. Smart move.

Michael _is_ playing it safe. He's made assumptions about his and Jan's quote, unquote relationship before and he's always made an ass out of himself. That's why he doesn't want to assume they're gonna have all kinds of sex this week.

"Can I get you something to drink? I have eggnog or wine...?"

"Sure! Wine would be great." This should loosen her up a bit. Otherwise, it's gonna be a long week.

Jan spent the last two hours in her car fantasizing about them. Who was going to make the first move? Probably her. Who was going to finish first? Again-probably her. She's been wanting this since Chili's. Will they each strip off their own clothing or slowly take off each others? Maybe they'll just rip into each other. Since it'll all be such a blur, no one will really know who initiated it. Probably her, though. It's been a long time coming and it's obvious that they're gonna have sex. I mean, Michael said it's all inclusive. That's code, right? Then again, he's acting not _anything_ like she thought he would act. She's never been more confused by this man and that drives her crazy. She's definitely gonna have to make the first move. Yep. Otherwise it's gonna be a long, boring week.

An hour later and 2 glasses of wine down, Michael is giving Jan a very long, very detailed tour of his condo. He's loving every minute of the tour because it reminds him of "MTV Cribs" which Jan is also enjoying-thanks to the wine.

"Last stop of the tour…This is where the magic happens." He laughs as he opens his bedroom door. Jan is taking it all in. She was expecting it to look like a bachelor lived there. But it doesn't -Michael has a nice bedroom set. Even has some paintings on the wall. She couldn't help but think he probably just bought this stuff a day ago to impress her.

"So you can take the bed. I'll take the futon downstairs. We should probably get some rest, now. We have an early day."

"Oh Michael. You're not sleeping on a futon."

"It's okay Jan. It lays flat and is actually quite comfortable. Oh and I contacted the resort. I was able to get a separate room. That way you can have your own space and-"

 _It's time,_ Jan thought. "Michael-" Jan begins to slowly unbutton her shirt and slowly walks toward him, "-that won't be necessary." Her shirt falls on the floor revealing her black lace bra.

"Whoa."

"We both know what "all inclusive" really means." She managed to slip her pants off revealing her matching black lace thong.

"What are you doing, Jan?"

"Something I should've done a long time ago." She pulls Michael in close as she kisses him softly and tenderly. Once she has his attention, the kiss deepens as they both allow each other in. _Now I think we're on the same page._

After they both finish, they lay there in silence and in shock at what just happened, still trying to catch their breath. Jan breaks the silence, "did you really book another room?"

"Nope." Jan and Michael both laugh. This was definitely the ice breaker they needed in order to have a fun non awkward vacation.

—

They arrive at the airport the next morning at about 4am. Both anxiously awaiting the very much needed vacation. They make their way to the bag check-in.

"Welcome to Delta-how many bags will you be checking in?"

"Two please."

"Alright sir-if I can just see your guys' passports?"

Jan already has hers out and opened for her and puts it up on the counter. Michael, on the other hand isn't quite as organized and is digging his out of his carry on.

"So…vacationing in the lovely Sandals, Jamaica, huh? It's so beautiful there. How long have you guys been together?"

"Oh well I…uh guess...what?" Michael looks at Jan, "um 4 or 5…5 hours, I think? This is my boss, so…"

"Ah…got it." She didn't get it. How does that explain anything, really?

As Michael keeps searching for his passport, "so I heard about this club you have and was wondering if there was a way to upgrade and how much it'd be to upgrade?"

"I'm sorry-are you talking about first class? It looks like you're already sitting in first class."

"No it's not first class. It's called 'The Mile High Club'? I don't know…I just heard about it and-"

Jan nearly chokes on her own spit while the lady blushes and smirks a little.

"Oh I uh…"

"Does Delta not offer-"

"Michael-I'll explain it to you later, just give her your passport." Jan and the lady both laugh.

"What? Is that like super exclusive or something?"

"No-just hurry so we can go."

As they head towards security, Jan is still smiling at how naïve Michael can be sometimes.

"I don't get it. What's the mile high club? Oh! Okay…I am so dumb…"

"Get it now?"

"Yeah-getting high a mile up in the sky?"

"Oh my god no. Michael- okay fine, it's-" Jan gets a little closer to Michael's ear and talks quietly. "The mile high club is people who have had…sex in the airplane bathroom."

Michael giggles, "oh! That's kinky. Oh wow! Seriously? People actually…"

"Well _I_ haven't, but yeah…maybe? I don't know. I think it's something you see on movies. I mean 1-how could that even be possible? Those bathrooms are so small. 2-It'd be impossible to keep quiet too. And 3-it'd be hard to sneak in the bathroom together. Flight attendants are everywhere, people would bound to notice. I don't know-it's stupid."

"Maybe that's the thrill of it? You know? Getting caught? What do you say, Jan?"

"If you're suggesting you and I um... I will already tell you-it ain't gonna happen. Who-by the way-were you talking to who is a _member_?"

"Todd Packer."

"Oh yeah right. Michael! The guy could hardy fit in the bathroom by himself let alone having someone else in there. Remind me how you two are friends again?"

Michael shrugs and laughs again. He still can't believe Jan is next to him….by choice.


	3. Michael the salesman

Michael the salesman

Michael and Jan have been on the plane for a couple hours now. Jan is sitting next to the window. She fell asleep for just a little while when she woke up to the sound of Michaels voice. He was chatting it up with the guy next to him. Poor guy. However, the guy he's taking to doesn't seem disinterested in Michael.

"What are you going to Jamaica for…business or pleasure?"

"That's what she said." Michael loves using his 'classic' lines on people he's just met. The man next to him smirks a little, "it actually depends on who you ask, right Jan?" He rubs her thigh. Jan is not sure what to say-she just stares at his hand on her and feels _excited_ a little, "this is my boss actually, so…"

"Ah…okay." Again…how does that explain _anything?_

"It's not what you think. Totally mutual." Awkward silence fills the air which Michael surprisingly notices and changes the subject. "So what kind of work are you in?"

"I am a rep for Georgia Pacific. How exciting, right?"

"Oh my goodness! Are you kidding me? That's awesome…we-"

"No one has ever been this excited for what I do before."

"Alright, let me ask you this. Who is your main supplier? Office Depot right? Now let me ask you this. Did they lure you in with their low prices and quick delivery? Oh and let me guess, after you were with them for what-6 solid months, they jacked up the prices, delivery takes longer and they now actually charge you an arm and a leg for two-day shipping but you're stuck with them because you signed a two year contract with them?"

This man, let's just call him Dave, and Jan are left absolutely speechless. Both in completely different ways.

"Holy shit-it's scary how dead on you are. How did you know all that?"

"I just so happen to work at this paper company called Dunder Mifflin. We _may_ be mid-range but we are top-dog when it comes to everything with price, delivery and customer service. We lock you in at a price that won't ever change for you. We value our clients and loyalty is everything to us."

"Wow. That sounds fantastic. How have I never heard of you guys before? Do you have a card? I would love to get together with you when we get back."

"Yeah…absolutely." As he reaches in his back pocket, he looks at Jan, smiles and winks.

Jan couldn't believe what she was hearing. She's so amazed and stunned, she can't even show any expression. Is he actually making a sale right now? He's making it so hard to resist him. He's also making it so easy to want him.


	4. Michael only has eyes for Jan

Michael only has eyes for Jan

The next morning, Jan wakes up before Michael. She makes some coffee and sits outside on their patio chairs. The sound of the ocean's waves calms her. The wind in her hair makes her feel at peace. She smiles as she day dreams about the night before. She still can't believe she's here. And with Michael of all people, but (and that's a BIG _but_ ) he's been amazing and she couldn't imagine being there with anyone else.

Which makes Carol pop into her head. She can't help but frown a little and almost gets upset at her for being an idiot for leaving Michael. _She did leave_ him _right?_ She actually has no idea what happened between them and _before_ she said she didn't care about that... but now? She kind of wants to know everything. She doesn't picture Michael leaving a woman, so it had to of been her. Idiot.

Her thoughts are interrupted by Michael coming out to the patio. His hair is tousled and he still looks sleepy, but he has a smile on his face. Jan smiles at him. He makes his way over to give her a kiss. "I think I could get used to waking up to your beautiful smile."

"Mmm." Jan kisses him again, this time longer. "Carol is an idiot."

"Carol? Uh…okay? I mean, yeah she was a blonde and all but what…um…what made you-"

"I just want to know what happened. She threw this all away? And you've been anything but obnoxious and I don't know-she's an idiot for breaking up with you. Well I'm assuming _she_ broke it off."

"You're right. She was the one to break my heart. But I'm so happy she did. You have no idea. I would much rather have _you_ here anyway. Anyway enough about-"

"How did she do it? Was there something that actually happened?"

"You really wanna know?" Jan nods. "I mean…maybe I was moving too fast. I probably cross the line but I don't know-I kinda liked her and I liked that she wanted to be with me sometimes. We had only been dating for 4 months, I invited her here which she declined and..." Michael pauses and takes a deep breath before continuing, "I photoshopped me in a picture of her and her family on a ski trip and wanted to send it out as our Christmas card. I put my head on her ex husbands body. Yeah she didn't like that…"

"Wow. Okay-well I would not have guessed that."

"Yeah…she thought it was weird. I don't know-maybe she's right."

"I mean, at least go to Jamaica first!" Michael and Jan laugh. "What an idiot. Well I am so thrilled she ended it."

"Me too, Jan. You have no idea."

This is Michael and Jan's 1st full day in Jamaica. They're getting a little more comfortable with each other as time goes on and with each drink they have. Sex was better last night than their first time, which was also amazing, but the second time felt more real and comfortable.

They're walking along the beach when Jan notices this _hot_ woman passing by. She's tall, blonde, skinny and has huge boobs that look completely fake. Jan's disgusted at the sight of her and just waits for Michael to check her out and make some immature comment.

As if on cue, Michael turns to her and pulls her aside. Jan rolls her eyes slightly, preparing herself to hear whatever stupid comments about that woman he has to say. Richard would never miss an opportunity to make a lewd comment- about her boobs none the less. Then later, when they'd be having sex, something about it made Jan feel like he was fantasizing about that bimbo.

Michael takes Jan's hands and smiles, "I am so lucky to have you here with me. Seriously, you are the most beautiful woman on this planet. Thank you for saying yes."

Well that took an unexpected turn. Again, Jan is left speechless.

"Are you okay? You're not regretting coming are you? I'm sorry, I know it was inappropriate asking you to come here and I know we're breaking like SOOO many rules but-"

"I'm sorry-I just, heh, I just thought you were going to make a comment about that woman that just passed us." Jan motions behind her but Michael sees no one. Just Jan. She blushes and can't help but feel embarrassed by her feelings. That's why she hates talking about them.

"Oh. Would _he_ do that or something?" It was very clear as to who _he_ Michael was referring to. "Jan." He rubs her hands with his thumbs, "believe it or not, but we're not all tools like Richard was okay?"

Jan once again kisses him.

Carol is an idiot. So what if he made a little Christmas card that was photoshopped? At least he's loyal. At least he's faithful. Any woman would love that.


	5. Michael is so thoughtful

***Warning*** This chapter contains come rated R material. This is probably the only chapter that will have that. I don't think it's worth it to rate this whole story 'M' so I hope that's okay with everyone

Also-are you enjoying this? I would love to hear you what you have to say about it because it makes me motivated to get more chapters written. Thanks for reading!

Michael is really thoughtful

Michael and Jan are taking their routine sunset walk along the beach. Normally, Jan would gag at how cheesy this was, but she quickly grown accustom to it. Mainly because…I mean, how could she not?

"Michael, where are we going? What are-"

"Chillax, Jan. I just want to see what's behind these huge rocks."

"I don't know about this, Michael. I'm starting to see black sand. I don't think we're supposed to be out this far."

"Shhhh-just trust me. Since when are you a rule follower?"

Michael climbs over a few rocks before reaching his hands out for Jans to help her over. She manages to get over and loses her balance which causes her to fall into Michael's arms.

"Thank you."

"Of course-so I wanted to do something-" Jan gasps at the beautiful site in front of her, "-extra special for you. You're so amazing, Jan. This is just an ounce of what you deserve. I would give you the moon if I coul-"

"How did you…when did you…wh-"

"I had this idea in my head and the awesome workers helped me pull it off. They did a fantastic job, didn't they?"

The sight in front of them is incredible. There's a table set for two, rose petals everywhere, which are a hundred times more beautiful on black sand, a blanket laid out so they could look at the stars, and lights wrapped around a few palm trees. There are candles and wine and more lights stringing along the sides of the rock wall. They were completely alone.

"It's nothing, really. Just my way of letting you know how happy I am that you're here." Jan remains quiet, still taking this all in. Michael feels a little unsure if he overdid it or not. "Shall we?" He makes his way to the table and takes a chair out for Jan to sit down. She smiles slightly while her mind is going 100 miles a minute. She's mesmerized by everything this man has done for her and is admiring the beauty of this black sand beach.

Michael turns on a mixed cd he made the day before they left. The first song is _Awakening_ by James Morrison. He pours them some wine before finally breaking the silence, "I overdid it, didn't I? I'm sorry. God I'm so stupid! I should've known-"

"James Morrison is one of my favorite artist. I can't believe you're playing this right now. Wanna dance?"

"Of course." Their food might get cold but he couldn't care less. When Jan Levinson asks you if you want to dance, you dance! He's gets up and takes her by the hand. His left hand finds her lower back as her right hand drapes over his neck and naturally begins playing with his hair. Michael's right hand finds her left and holds it close to their chests as they begin to sway to the rhythm of the song.

 _I haven't felt this awake in years_

 _Too busy to my tears_

 _To feel the sun was shining on my skin_

 _Locked up in my own cage_

 _Filled up with a bitter rage_

 _I couldn't see the prison I was in_

This song couldn't explain Jans feelings any better if it tried. She is still astounded as to how Michael chose _this_ song and the be the first one on the cd. Then again, she used to listen to the whole album constantly and almost every song meant so much to her on a different level. This song especially speaks volumes. She's been fighting these feelings for Michael aka _locked up in my own cage_ because she was scared and even ashamed to admit she even remotely liked this guy.

 _And I've been waiting for this awakening for so long, so long_

 _I gotta get a little light inside_

 _And I'm here holding out for just one thing_

 _And it's your love, your love_

 _It makes everything feel alright_

If you would've told her a week ago that she'd be head over heels for this guy, she would've told you that you were crazy, laughed in your face and told you that _she_ would be crazy if she felt any kind of love for Michael Scott.

But it happened. Here she was, _awakened_ , just like James was singing about. She thought that the only feelings she had for Michael were sexual but after the second day, those feelings began to grow immensely. This is the perfect moment to tell him.

 _And I walked across the line alone_

 _To find a truth I never ever known_

 _The truth was there all this time_

 _The only one who couldn't see was me_

"Michael, um-I think we need to uh have that talk now. You know? That talk we've been avoiding this whole trip?"

Michael has been dreading this talk since inviting Jan. It's not like he didn't know it was going to end. With Jan, nothing can ever continue. Nothing can ever just be perfect. Everything has to be logical.

Michael groans as if he's in pain, "no! I don't want to." He stops dancing and backs away from Jan.

Jan is taken aback by his childlike behavior which she hasn't seen all week, "Michael! We need to discuss what's going to happen when we get back!"

"There's that corporate Jan again! What the hell Jan? I thought we were having a good time. I did all of this for you and now you want to finish our last couple days by being depressed? Why can't we just live in the moment…mon?"

"Ugh you know what? Fine! I don't know what I was thinking having an actual adult conversation with you. I'll be in our room." She starts walking away but stops as her eyes begin welling up and a lump in her throat begins to form. She quickly regains herself and holds the tears in.

"Sorry- but I just don't need to hear the same shit. I know what you're going to say. Yeah I know! We can't continue this. This never happened. Don't tell anyone. What else? Oh! My favorite one-this was all a mistake!"

Jan looks back at him and glares at him. "If you know

Michael takes a deep breath, calms down and remains quiet, "I shouldn't have done all this. I scared you off-just like Carol. God! What the hell is my problem? Why do I-"

"Stop! Okay? Just stop talking for one minute!" Jan takes a deep breath to help her calm down, "I'm sorry. I really shouldn't have approached this conversation the way that I did."

Michael is still taken aback a little doesn't know what to say. He still thinks Jan is going to end it now versus later. She's the most confusing woman on this planet. That's what makes him love her so much. He just wishes she felt the same. "I knew this was going to end sometime and I tried to prepare for it but I just can't and I don't want to do this."

"Michael?" Jan gently takes his hands in hers and smiles as she tries to make eye contact with him. He finally looks her in eyes with those big, sad, green eyes, "I can't begin to tell you just how much fun I've had this week. I don't remember the last time I laughed this much or smiled even."

"Buuuttt…."

"No buts, Michael. Look, I know you think that I'm gonna say all those things and yeah-I guess you have every right to think that, but the truth is Michael? I'm supposed to be in Scottsdale visiting my sister right now but I canceled. I canceled right after I got off the phone with you. And I haven't seen her in over a year! Why the hell would I do that if I didn't want to be with you? Everything you did for me here is what made me want to have this talk with you. I'm actually falling for you. Something that used to scare me... but you're making this so easy." She ends by motioning the whole scene in front of her.

"Are you sure it's not just because we're on the island of love? Love is made here, Jan"

Jan smiles slightly, "first of all, we're on the island of land and water-Google it-and second...I've been fighting feelings for you since Chili's so I'm pretty sure that's not why."

Michael wraps his arms around Jan's waist, "so you're really supposed to be in Scottsdale right now?"

"Uh…yeah."

"But you came here…instead…with me."

"Yep…I sure did." She smiles at him and he follows with a giggle.

"Oh wow. Well _now_ I feel like a million bucks! Oh my god Jan...did you tell your sister _why_ you had to cancel?"

"I did." Jan nods and smiles.

"What'd she say?"

"She told me to be careful and…" Jan presses her breasts up against Michael and wraps her arms around Michael's neck, "…that she wants to know all the details. Well… _almost_ all."

Jan kisses him with fervor. She holds on to him tightly as his arms go every which way. She hastily rips open his white button down shirt and he lifts up her tank top. Butterflies enter her stomach with the touch of his hands on her. His fingers lightly travel from her waist up and he slowly removes her shirt. She does the same with his shirt and starts kissing his neck, then his collar bone, then his chest, all the way down to his buckle. She quickly loosens it and tugs it off. She continues by unbuttoning his pants, but then he stops her. She gets back up and finds his lips again. He tugs on the tie of her maxi skirt to loosen it.

They find their way to the blanket to lay down. Michael mimics Jan's prior behavior by kissing her all the way down to her skirt. More butterflies enter her stomach when his tongue dips into her navel. His fingers trace the hem of her loosened skirt and his hand slips under. He lightly strokes her wet underwear while she moans in pure ecstasy. He maneuvers her skirt off.

She grabs onto his shoulders as he begins kissing her inner thigh. "Oh god!" He makes his way his way back up to her soft lips. She quickly takes his pants off and climbs on top of him. She begins riding his harden shaft. He takes control once again and rolls her back onto her back. They both take off their last item of clothing before Michael positions himself back on her. He enters her and naturally Jan moans. With each thrust, her moans gets louder and more satisfying. Their rhythm is in sync and the pace quickens as they both orgasm at the same time. "Oh god!" "Oh fuck!" They take a minute to look into each other's eyes. Michael gets off her and they both lay there trying to catch their breath. They both lay there as the music continues to play, the candles keep burning and their food keeps getting colder. They're both shaken, unable to move, still coming down from that orgasmic episode.

"If you would've told me a week ago that I'd be _here_ in this moment with _Michael Scott,_ I would've laughed in your face. But here we are, making love on a black sand beach in Jamaica, and not regretting a second of it. Thank you, Michael. Thank you so much for inviting me."

"All I heard was _making love_ "

They both laugh as Michael holds her closer.

 _You and I_ by Tom Walker begins playing

 _Let's get drunk_

 _I'll pour my heart out through my mouth_

 _This year's been hard for us no doubt_

 _Let's raise a glass to a better one_

 _And all the things that we've overcome_

 _Are bring home to us 'cause_

 _Me and you we can hold this out_

 _Only you understand how I'm feeling now yeah_

 _And I know I can tell you anything_

 _You won't judge, you're just listening yeah_

' _Cause you're the best thing that ever happened to me_

' _Cause my darling you and I could take over the world_

 _And one step at a time, just you and I (just you and I)_

' _Cause you're the only one who brings light just the sun_

 _One step at a time just you and I (just you and I)_

 _ **Hope you liked it! I recommend listening to those songs that were in this fic. I have a hard time not thinking about Michael and Jan when I hear them.**_


	6. Jan Limbos

_You Would Not Believe How Low This Girl Can Limbo_

Jan has impressed Michael in way more ways than just the one. Just her being here with him is impressive enough. Her opening up to him is impressive. Or slamming down shots like they're going out of style…that's _super_ impressive. Her acting like how girls act when they're in a new relationship. She can't keep her hands off of him. And it's not even all in a sexual way-no-it's like super boyfriend/girlfriend, newlywed like. Just the simple little kisses she gives him (which-to Michael-isn't _just simple-_ this _is_ Jan, after all _)_ or how she places her hand on Michael's thigh as she's laughing hysterically at something he just said. Oh, and this is all done in public. Not just in their room. All of those things make Michael more than just impressed-it makes him feel a stronger connection with this woman than he ever thought possible. There's a little something about Jan that he doesn't know, however, and he's about to find out.

This is Michael and Jan's last night in Jamaica. They're right outside the lobby bar waiting for the night activities to start. They've had enough drinks to make them feel buzzed but not enough to make them forget this night.

Jan is especially excited about tonight because tonight's activity is the limbo. She's finally going to be able to show someone this talent. No one knows this about her, but she can limbo so low you'd think every limb in her body was disjointed. Michael lives for shit like this which is why she's excited that he'll be the one who gets to experience it. She wouldn't want it any other way.

Jan laughs, "I still can't believe you got that."

Michael laughs as he waves his "braided" hair and beads around. "I know. Gotta give the ole peeps at the office something to talk about."

They laugh once again before Michael lowers his voice and gets closer to Jan's ear, "Let's go back to our room. Come on-I want to…" he whispers something in her ear which makes her giggle and eyes widen a bit. "What do ya say?"

"Oh Mr. Scott-you are so bad." He giggles as he gets up with her hands in his. Jan, however pulls him back to sit down.

Jan keeps her voice quiet, "Actually, Michael. As much as I…want you to do those things to me, I have been waiting all week for this night. Can we just stay and um…watch this? Then we can go back to our room and I'll…" same thing-Jan whispers in Michael's ear which makes _him_ giggle.

"That's what she said."

The MC begins talking, "How's everyone doing tonight, mon?! Okay so tonight we're doing one of my favorite activities-the limbo! Who here is a good limbo-er?"

You can hear some screams come from the audience. Jan and Michael look at each other and laugh. "Can you limbo, Michael?"

"Not even a little bit." They laugh again.

"So tonight's winner will win this awesome steel drum! The lowest limbo-er will be able to bring this beauty home. Sounds pretty irie, huh mon?"

"Holy shit! That'd be so awesome! I've always wanted one of those. Okay, well since we've been here-"

MC continues, "everyone is eligible to play so if you think you have what it takes to limbo so low, you appear boneless, then get your ass on up here."

Jan gets up from her seat.

"Where are you going?"

"You know how I really wanted to see this activity tonight?"

"Um…yeah?"

"Well it's not because I want to watch people make an ass out of themselves."

"It's not?"

"Nope." Jan smiles before kissing him, "I'm gonna win you that steel drum."

She heads up to the stage where there are about 10 people. Michael is left speechless, something that is rare for him. He can not wait to see how low Jan can limbo. He already knows she's gonna win-she's perfect at everything.

"Okay so how about everyone say their name, where they're from and how low they think they can go."

Jan is stretching a little while everyone goes before her, she straightens up when it's her turn, "My name is Jan, I'm from New York City and I can limbo lower than the pegs on the stand."

"Wow! Seriously? Who are you here with?"

"Well I uh guess my boyfriend?" Looks out to Michael, "right? Is it-is it safe to say that's what we are? I'm his boss, so…"

"Oh I see…" he didn't see. "Well he is a lucky man, I'll say." The MC finishes with a wink and Jan blushes. "Alright mon-let's get started. Would you like to start us off Jan?"

So of course the first couple "rounds" are easy, even for the amateurs. There are always that one or two who hit bar right off the bat. It comes down to Jan and this other woman-who is a yoga instructor. They are on the 2nd to the last notch. Jan goes under with ease. It takes time and concentration but she does it. Everyone cheers and Michael has the biggest grin on his face. He's so proud of his girlfriend. The yoga instructor begins. She follows suit by taking her time and concentrating really hard. She ends up losing her balance half way through and falls down. People in the audience "Awww" at her but clap at how well she did then clap harder as the MC takes Jans hand and raises it in the air, indicating her triumph. Michael rushes up to the stage with a huge grin and pride. He can't wait to bring her back to their room.

"I'm not done yet." That's the truth-she's not. Michael stops at the bottom of the stage and his smiles fades a little. She had to prove it to everyone that she could go lower than the lowest notch.

"You won." The MC reminded her.

"I know…but I told you I can go lower than the pegs, so I will go lower than the pegs."

"Alllllright! Dedication and commitment…I love it."

Jan stretches just a tad more. "Alright-let's go." She says as she cranks her neck from side to side. Jan continues to show everyone her talent. Everyone, including the yoga instructor, is impressed. After it gets to the last notch, Jan motions for them to bring it even lower. After lowering it a few more times, she finally falls on her back, which isn't that far off the floor anyway. She begins laughing and everyone starts applauding. Michael rushes to her side and joins her by kneeling down. He kisses her and calls her _crazy_ and _inhuman_.

"There ya have it folks-the lowest limbo-er we have ever seen. That was sure humanly impossible."

People laugh while Michael helps Jan up. People cheer once again and the MC hands over the steel drum.

They begin heading back to their room. Jan's on such a high right now. Her adrenaline is off the charts. Michael is not only impressed but also so incredibly proud of her. And amazed. Amazed at not only how low she limbo-ed but the fact that she won the steel drum for him. Not her. Him.

They get to their room and Jan closes the door and leans back on it and sighs. She's tired and sore. Michael smiles at her and she returns a smile. He grabs her by the hands and leads her to the bed.

"You need a hot bath and massage."

"I can't tell you how thrilled I am for being able to share that talent with you."

"Tell me about it. I live for shit like that…especially from you. Come here." He takes her in his arms and every bone in her body relaxes. "Let me get the bath water going. You need to relax those muscles. And then I can give you a full body massage."

"Oh god, that sounds amazing, Michael." She kisses him passionately.

"Do you need to have an ice bath like the athletes have? I mean no normal human can bend their body like you just did."

Jan laughs, "A hot bath would be just as good. Thank you."

Michael stares at her in awe and smiles as he shakes his head. She blushes a little but smiles back.

"What, Michael?"

"Oh, I just can't believe Jan Levinson is standing in my hotel room. It's a dream come true."

Jan laughs that beautiful laugh of hers, "I'm just a person Michael. Just like you. I have needs and wants and goals in life. Just like you."

"You're not _just_ a person Jan. You're the hard on the outside, soft and gooey on the inside, ice queen, Jamaican sun princess."

"Oh god Michael." Jan rolls her eyes at his infatuation with her.

"Seriously Jan! I can't help but feel so…so… _honored…_ to be able to see this side of you. I just…"

"I know Michael…I know." She smiles as she kisses him. "Now for the love of god, please make me that bath."


End file.
